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Villa holiday rentals in Castellina in Chianti

Find and book unique villas on Airbnb

Quick stats about villa rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti holiday rentals start at $127 SGD per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

  • 4.5 Average rating

    Castellina in Chianti stays receive an average rating of 4.5 out of 5 from guests

Top-rated villa rentals in Castellina in Chianti

Guests agree: these villas are highly rated for location, cleanliness and more.

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Guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.93 out of 5 average rating, 255 reviews

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

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Superhost
The exterior of a charming stone villa is showcased, with a refreshing swimming pool in the foreground. Lush green grass surrounds the pool area, and a shaded gazebo with seating is positioned nearby. Rolling hills and a clear blue sky form a picturesque backdrop.
Villa in Greve in Chianti
4.85 out of 5 average rating, 179 reviews

Villa La Doccia, Greve in Chianti.

Villa La Doccia si trova a circa 8 minuti di auto dal centro di Greve in Chianti, in Località Casole, nel cuore della splendida campagna del Chianti. La villa è situata in una zona tranquilla e silenziosa, all’interno di una piccola azienda agricola circondata da vigneti e uliveti, dove gli ospiti possono godere della natura e dei tipici paesaggi toscani. La posizione è ideale per chi desidera rilassarsi immerso nella campagna ma allo stesso tempo essere vicino al centro di Greve in Chianti

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Top guest favourite
A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.
Villa in Barberino Tavarnelle
4.97 out of 5 average rating, 106 reviews

CasaDiManuela:TotallyPrivateChiantiVilla withTub

CasaDiManuela:TotallyPrivateVilla in Chianti withTub Jacuzzi The villa, immersed in the Chianti countryside, was obtained from an old farmhouse and then renovated with extreme care and attention to detail. Original terracotta floors and ceilings with ancient exposed beams, old traditional Tuscan furniture, flowery fabrics that dress beds and armchairs, paintings, antique china and lived objects recovered from markets and junk dealers will frame your living room. Nothing here is by chance.

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Guest favourite
Villa in Monteriggioni
4.97 out of 5 average rating, 174 reviews

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

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Top guest favourite
An aerial view captures the charming layout of ancient stone houses surrounded by lush greenery and cypress trees. A swimming pool is visible, accompanied by well-maintained gardens featuring various relaxation areas. The surrounding landscape reveals vineyards and rolling hills typical of the Chianti scenery.
Villa in Castellina in Chianti
5.0 out of 5 average rating, 17 reviews

I CIPRESSINI DEL CASTELLACCIO (Cip 1 + Cip 2)

Barn and stone house with swimming pool and stunning views in Chianti Classico The Cipressini del Castellaccio are ancient stone houses, originally agricultural annexes to the main farmhouse dating back to the seventeenth century located in the heart of the Chianti Classico on the side of a slope with a breathtaking view of the Val d.Elsa. Luxuriously renovated and furnished, equipped with every comfort, they are located in such a way as to guarantee absolute privacy.

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Top guest favourite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa
4.95 out of 5 average rating, 202 reviews

Il Vichiaccio: Florence Villa with Jacuzzi

Cozy Chianti Villa near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!

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Top guest favourite
The villa is depicted with a stone exterior, surrounded by olive trees and rolling vineyards. A circular pool is featured in the foreground, offering a tranquil spot for relaxation. Umbrellas provide shade over lounge chairs nearby, enhancing the serene outdoor space.
Villa in Radda in Chianti
5.0 out of 5 average rating, 33 reviews

Villa con piscina nel Chianti - Castellare Petroso

Situata nel cuore del Chianti Classico, tra vigne e boschi, Castellare Petroso offre un’autentica esperienza toscana, sobria ed elegante. La villa in pietra di galestro è immersa in un parco recintato di oltre 5 ettari, garantendo massima privacy e relax. Un cancello automatico all'ingresso principale accoglie gli ospiti in questo scenario unico, dove l'architettura si fonde nel paesaggio splendido e selvaggio. Un rifugio esclusivo per chi cerca la vera Toscana.

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Top guest favourite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa
4.97 out of 5 average rating, 119 reviews

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

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Superhost
A well-appointed villa is situated on an open ridge, surrounded by lush greenery. The private pool, equipped with sun loungers, is framed by vibrant gardens. The structure combines rustic charm with scenic views of the Tuscan landscape, offering a tranquil retreat.
Villa in Castellina in Chianti
4.92 out of 5 average rating, 12 reviews

Casanovina

Casanovina is a beautiful holiday villa in the Chianti region, set on an open ridge with spectacular views over the typical Chianti Classico landscape. Just a few hundred meters away is the renowned winery Castellare di Chianti, and the charming village of Castellina in Chianti can be reached in about 25 minutes on foot. This property is perfect for a large family or a group of friends wanting to spend relaxed days together.

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Top guest favourite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta
5.0 out of 5 average rating, 189 reviews

La Torre

Antica villa toscana, bellissima, con giardino privato esclusivo, completamente ristrutturata, immersa nelle splendide e dolci colline toscane. La villa ha una vista mozziafiato, molto soleggiata, ben arredata e dotata di tutti i comfort, silenziosa e non isolata. La casa si trova a Bagnolo, piccola frazione di Impruneta alle porte del Chianti, zona di uliveti, vigneti e pace. La casa si trova a circa 10 km in macchina dal centro di Firenze.

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Guest favourite
Villa in Monteroni d'Arbia
4.95 out of 5 average rating, 171 reviews

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

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Guest favourite
Villa in Siena
4.89 out of 5 average rating, 307 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

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Popular amenities for villa rentals in Castellina in Chianti